The present invention relates to 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones produced by the process more particularly disclosed and claimed in copending application for U.S. Letters Pat. No. 819,889 filed on July 28, 1977, now U.S. Pat. No. 4,096,158 (Title: "Process For Preparing 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones") and novel compositions using one or more of such 5-acyl-2-(furfurylthio)dihydro-2,5-dialkyl-3-[2H]furanones or "cis" or "trans" isomers thereof to alter, modify, augment or enhance the flavor and/or aroma of consumable materials or impart flavors and/or aroma to consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors to (or in) various consumable materials. These substances are used to diminish the use of natural products, some of which may be in short supply and to provide more uniform properties in the finished product. Coffee-like, roasted, cocoa-like, caramel-like, licorice, and roasted almond aroma and flavor characteristics are particularly desirable for many uses in foodstuff flavors, chewing gum flavors, toothpaste flavors and medicinal product flavors. Sweet, caramel/coffee aromas and flavors prior to smoking and sweet, caramel/coffee, nutty/pyrazine and roasted nutty aroma and taste characteristics on smoking are particularly desirable in tobaccos as well as tobacco flavoring compositions and in tobacco substitutes and flavoring compositions for such tobacco substitutes.
When one mole of diactyl is reacted with one mole of furfuryl mercaptan a coffee flavored reaction product is produced which has been discovered by us to contain a small percentage (about 10% by weight) of 5-acyl-2-(furfurylthio)dihydro-2,5-dimethyl-3-[2H]furanone with one of the "cis" -- "trans" isomers being in a ratio to the other of the "cis" -- "trans" isomers in about 2:1. The process for preparing such a reaction product (without describing the constituents of the products) is set forth in Swiss Pat. No. 128,720 published on Nov. 16, 1928. It is stated in the example at column 2 on page 1 thereof that when one mixes furfuryl-2-mercaptan and diacetyl the product (alpha-oxy-alpha-acetylethyl)furfuryl-2-sulfide is produced. There is no disclosure in Swiss Pat. No. 128,720 that an additional mole of diacetyl added to the resulting reaction product will produce the compound having the structure: ##STR5## or any of its "cis" or "trans" isomers having the structures: ##STR6## In addition there is no disclosure either explicit or implicit in Swiss Pat. No. 128,720 that the compound having the structure: ##STR7## can be produced having a very high intensity and long lasting aroma and taste characteristics of the nature described herein.
U.S. Pat. No. 1,696,419 issued on Dec. 25, 1928 (Title: "Method of Producing Artificial Coffee Aroma") discloses the production of a coffee flavor using:
"One part of diacetyl, four parts of acetyl propionyl, four parts of methyl ethyl acetaldehyde, three parts of acetaldehyde, two parts of alpha methyl furfural, one part of furfural, three parts of pyridine, two parts of isovaleric acid, one part of phenol, one part of isoeugenol, 0.5 parts of guiacol, 0.5 parts of alpha methyl cyclopentenolone, 0.6 parts of methyl mercaptan, 0.3 parts of furfuryl mercaptan, 0.3 parts of n-octyl alcohol and 0.4 parts of thioguiacol"
at page 3, column 1, lines 29-39.
The compound having the structure: ##STR8## is not indicated to be produced as a result of admixing at higher temperatures the foregoing ingredients.
Nothing in the prior art discloses the reaction of one or more dimers of alpha, beta diketones having from 4 up to 6 carbon atoms with furfuryl mercaptan to form the genus of compounds having the structure: ##STR9##